Rose Garden Drabbles
by SquadronGal
Summary: Some random Ruby X Oscar stories I write down sometimes :)
1. Chapter 1: First Kiss

Rose Garden (Ruby X Oscar): First Kiss

The waterfalls of Mistral hummed white in the distance. He could feel the warmth radiating from her, and saw the moon reflecting ever so perfectly from her silver eyes like glass. In such pale light, Ruby Rose looked absolutely ethereal. As they inched closer to one another, Oscar seemed to have completely forgotten of the disembodied voice in his head. The one known as Ozpin seemed to have fallen completely silent, and Oscar gratefully embraced the solitude.

Her breath smelled of chocolate…

His lips met a sudden softness, hazel eyes opening rapidly to see that he had been paused by Ruby's fingers, thin but rough from ware. Their gazes met, silver orbs squinting up at hazel ones as if the contact put them in physical pain.

"I'm sorry." Ruby muttered dropping her hand. Oscar's heart sank.

"D-Did I do something? If I did just tell me. I never wanted t- "

"No, it's not you I promise." Ruby's gaze fell to the stone walkway beneath their feet. Her hands intertwined with one another, quiet and reserved. The moon no longer reflected in her gaze, but sadness instead.

"It's just… there's so much going on in the world right now. Things and people that are making it less of a safe place." Oscar caught her clenched hands tightening. "We've lost… a lot of people close to us. And some of us have suffered terribly from those losses." She laughed, hollowly. "And here I am worrying about whether or not you- "And before thought is processed, her sentence stops.

The two were left in a sad silence, dark shadows of the city street slowly creeping in. Oscar wondered if Ruby felt as discouraged as he did, not just at the sudden interruption, but at the tragic truth behind it all. Here were two children with the weights of responsibility thrust upon them, and as the world expected them to take action, here they stood precious hours of youth ticking away as they both yearned for nothing more but closeness between the them.

But alas, what were two children to do?

"I'm so sorry." She repeated shaking her head. "But there are things we need to settle first. That _I_ need to settle first." She looked up at him, desperately. "Do you understand what I'm saying?"

Oscar nodded.

"I do." In that moment, Oscar had no recollection of the world around him. The truth of Ruby's words rang in his ear, but the moon called to him louder and clearer, beckoning him. He knew well should he not follow through, the moon would surely set, perhaps never to be seen again. His strides are swift, and she blinks.

All at once, Oscar is suddenly made incredibly aware of how chapped his lips are when he presses them against Ruby's, both of which share a softness to something like rose petals. His worn glove presses ever so gently against her cheek and for a moment he silently curses not being able to feel her skin.

After no less than a beat, Oscar slowly withdrew, both his breath and Ruby's being lost to the wind.

"Just in case I never get that chance again." He smiled, cheeks reddening under the moons gaze, under her gaze. Ruby smiled as well, as the aura between the two shifted from an air of disappointment to that of a tranquil peace.

They both walk back to their hotel, side by side. Not a word is uttered, nor is one needed.


	2. Chapter 2: Physique

There is an age-old question asked amongst huntsmen and huntresses for generations; which is sharper, the beowolf's fang or its claw? As of late Ruby Rose can say with absolute certainty that it is its teeth.

True, Oscar Pine had only just recently joined in on the whole fighting grimm for the sake of humanity thing. And while he originally had taken to it like a pro, the strength of his aura left something to be desired. It was recently tapped, but who or what no one was certain, but it certainly didn't have the same amount of strength as the rest of the experience team RNJR and Qrow.

He had endured the first swipe of the beowolf's claw just fine, but hadn't reacted in time when the thing bit right through his aura shield and his shoulder, leaving the boy a bloodied mess. Ruby had made quick work of the beast after that. Thankfully however the wound itself wasn't a deep one, and with an expert patch job done by Ren, Oscar was steadied and assisted back to his hotel room in Mistral.

Qrow carried him by his right shoulder, with Ruby carrying his stuff close behind despite the elder gentleman's insistence that she didn't have to.

"No really. You really don't have to." Qrow reminded his niece, emphasizing every syllable of every word as the three approached the doorway to Oscars room.

"He's right…" Osacr weakly muttered out "you don't have to."

"Your scar is still healing," Ruby stated at her uncle, then turning to Oscar "and you can barely stand up straight." She adjusted her hold on Oscar's bag, gripping the hilt of his cane in her first. The boy smiled thankfully as Qrow merely rolled his eyes, slamming the door open and tossing the boy onto his bed. He hissed upon impact, clutching his wounded shoulder.

"Uncle Qrow!" Ruby scolded, setting down the boy's things and sitting him up slowly. Qrow couldn't help but scowl at the fact that she cared so much about the hayseed. He was being a complete wimp. Ozpin would have shaken a wound like that right off. Some successor…

"You'll need some medicine for those bite marks so they don't get infected. I'll go nab some from the inn keeper and some more bandages." Qrow turned, about to make his way out the door. "Try to keep him conscious for me, kiddo."

The door closes with a small click as Oscar sticks his tongue out at it, earning a small snort from Ruby.

"Come on, grumpy." The hooded girl teases bouncing up to her feet "I'll go get a washcloth and basin."

"What?"

"If we're changing your bandages we need to wash your shoulder first. Stay here I'll be right back."

"Umm, sure."

Admittedly, the rooms in the hotel weren't nearly as nice as the dorms back at Beacon, the bathrooms even less so, but Ruby scavenged what items she could from the practically bare necessities of the room's bathroom. A single cloth meant to provide as a hand towel, and a bowl found under the sink cabinet. Fill it up with water and, bingo! Nurse Rose was ready for action!

With the filled basin, Ruby gentle bumped the bathroom door ajar with her hip, stepping carefully as not to spill any water as she carried both basin and towel through the door and into-

"…"

Tanned skin was the first thing Ruby noticed upon entering the bedroom again. Stout shoulders flexed as his stained shirt was pulled over head landing in his lap. Right next to the now resting fabric were toned abs heaving in pained breath along with a robust chest slightly bloodied from the left side…

Ruby snapped out of her tranced when she felt the sprinkle of water on her tights, noticing she had tipped the basin just a bit.

"Oh hey." Oscar greeted upon noticing her presence.

"Hi." Ruby responded, dumbly. "Uuuhhh… oops." She stated, also dumbly as she called attention to her little mishap.

"Mind helping me with these bandages? Ren kinda tied them pretty tight…"

"Of course, … I mean no. No! I mean yes! Yeah! No. Yeah! Not as in 'Yes I mind' but as in 'Yes I will help'…with…that…"

She set down the basin on the night stand and began fiddling with the knot on Oscar's bandage. She noticed his skin was incredibly warm, it just radiated heat it seemed. Was that from the battle? Was that his natural temperature? She hoped he wasn't catching a fever too. The fabric came loose and fell from Oscars arm as Ruby undid the tie, gathering the soiled cloth in her hands and into the nearest waste bin.

The wound was still wet, though the flow had slowed significantly. The edges were swollen and red. A nasty gash to say the least… so why couldn't Ruby focus on that instead of Oscars prominent pecs? With almost too much eagerness she fetched the basin and cloth, ringing out the extra water and began dabbing at the bite marks.

The boy hissed at the contact, squinting in pain as Ruby cleaned off the dried blood from his collar bone.

"Sorry…" she apologized.

"You're fine" he replied, and for a split-second Ruby almost felt the need to reply with 'So are you.'

It took all her composure to keep her hands from shaking as she worked at Oscar's shoulder, all the while eyes wandering about his exposed torso. Her eyes traveled down to his abs again, and noticed he had the slightest hint of… a four pack? Okay, not a chiseled eight but damn did the subtly suit him. And all from just farming?

"Sooooo you farmed and stuff, right?"

Oscar raised an eyebrow, surprise by Ruby's topic choice.

"Yeah, I was a farm hand for my aunt."

"So what kind of stuff did you do?"

He shrugged "The usual I guess. Plowing, planting, hauling water, chopping wood…"

"Everyday?"

"Pretty much."

Wow. No wonder he was this well built. Oscar had begun rambling on about some story about feeding chickens which Ruby new she should try to pay attention to. But… just… couldn't… This was getting ridiculous, shirtless men were nothing new to her! Yang had pictures of shirtless guys hung up around their room all the time! But they were idols and celebrities. Blake's book had illustrations of several shirtless men on the covers. But they weren't real. Her dad would walk around the house shirtless all the time! But that was her dad. Jaune and Ren when RWBY and JNPR went to the pool together back at Beacon! But they're her friends. Oscar's also her friend, at least to her. But Oscar was also different… she wasn't entirely sure how but some way, somehow, he was different.

As Ruby had been running these thoughts in her head she had failed to even realize that in her deep thought her fingers had begun to trail along Oscars torso. Gently brushing the edge of the bandage around his neck and down his pectoral muscles like a feather. Upon reaching his abs she had begun to just mindlessly but gently poke at them. Solid. Perfectly solid…

"R-Ruby?"

Ruby snapped out of her daze immediately, looking up at Oscar who's face showed a _deep_ red. If he was at all sluggish before, he certainly wasn't now, and neither was Ruby Rose. She felt her face also heat up as she quickly withdrew her wandering hand, tucking it between her legs.

"I-I-I-I'M SORRY!" She covered her mouth after realizing her apology may have been a bit too loud. Both teens looked down at the floor, an awkward silence falling between them, landing at their feet.

The washcloth was sitting on Oscar's shoulder now, the bite marks on his shoulder much cleaner and less swollen than before. The cloth itself had been dirtied however, giving Ruby the conclusion that she should leave this painfully awkward situation by cleaning it in the bathroom.

As she reached for the cloth however, Oscars hand latched onto hers, his eyes looking at her held hand but not at her.

"It's… okay…" he let out. "You don't have to feel weird about it… I don't mind…"

There was a sincerity in his voice that somewhat put Ruby at ease. Their eyes finally met, silver orbs locked onto hazel ones, translating a message that said something along the lines of 'We're cool, but let's not tell anyone about this.' They both smiled.

Until Ruby noticed Oscars eyes averting followed by a good amount of color draining from his face. The girl turned and found her uncle, returned with medicine and bandages in tow, and a fire of furry burning in his eyes.

"Ruby, I need you to go get a glass of milk for Oscar."

"… Why…?"

"To hold his teeth in place until you get him to the dentist."


	3. Chapter 3: Keeping Count

At first glance one would assume Oscar Pine had no more than eight or nine freckles upon his face. But at a closer glance, one would notice that he had a multitude of smaller freckles aside from his bigger, prominent ones. Tiny flecks that faded into the depths of his tan pores. Ruby had on occasion glanced at the small sea of spots upon his cheeks, wondering and contemplating just how many of those tiny specks he possessed. Well today would be that day.

Oscar sat on the couch, flipping through the pages of a book he had slipped off the shelf and into his lap. The tiny bent glasses that once belonged to Beacon's headmaster sat on the bridge of his nose, slipping down the slightest bit only to be pushed up again by Oscars index finger.

 _"In one fell swoop the artifact was clutched in Stone's grasp, as he slid the jar on the pedestal. There was a moment of silence, leading the adventurer to assume the traps had not been set off yet until- "_

The words on the page were suddenly lost as Oscar felt the weight of the couch cushions shift, and Ruby sat next to him. She looked up at him with a small smile, as the boy gently wrapped his arm around her shoulder, returning to his book.

 _"The ground shook as a large boulder emerged from the wall, staring down Stone and beginning its slow roll. Stone tipped his cap, turning on his heel and bolted down the hallway as it crumbled around hi- "_

Another unexpected shift caused Oscar to lose his place as the ebony haired girl sat herself in his lap, facing him in a straddle. Ruby leaned against him, trapping the book between their stomachs momentarily before falling to the floor, and rested her forehead against his.

"Well hello there." Oscar greeted, humored by Ruby's sudden but not completely unwelcomed action. Pale fingers grabbed at the rim of Oscars glasses and set them aside, slowly lifting to glide over his cheek.

"One… two… three…four…five…"

"What are you doing?" Oscar asked, holding back a chuckle.

Ruby's tracing finger pressed against Oscars lips, eyes unwavering from the flecks on his face.

"Counting." She simply replied. The farm boy smiled, slowly picking up on her hints and letting her do what she willed. Her index finger pressed gently along his cheek as she mouthed the numbers she counted off in her head. Her gaze never met his, but that certainly didn't stop Oscar from getting lost in her fixated gaze. After all, her silver eyes, while deadly were two of the most beautiful orbs he had ever gazed upon.

For a short moment, he found himself giving thanks for moments like this, moments that allowed such a calm closeness.

Suddenly Oscar was pulled from his trance as he felt the warmth of Ruby's breath on his cheek bone. The numbers she had counted off in her head before now escaping her lips in barely audible breaths.

"15…16…17…18…"

"Having fun?"

"Ssssssshhhhhhhh. Don't make me lose count."

Oscar chuckled, causing Ruby to squint just the slightest bit as she kept her eyes on a fleck at the center of his cheek. He smiled, a sudden thought creeping into his head.

"Soooooo how many have you counted so far?" He asked, quickly pecking her nose.

"23." She replied, silver eyes meeting his for a split second before returning to crease between his nose and cheek.

"Mhmm." He nuzzled her nose with his. "Have you made it past my noes yet?" His lips pressed against her forehead. Rather than a response to his inquiry, Ruby simply continued to count off, voice slightly raised in an attempt to get a point across.

"26, 27, 28, 29…" Oscar pecked her left cheek, quickly moving to her right when she showed no response. "30, 31, 32, 33,…"

"That many huh?" He kissed both her temples, causing an audible protest from the girl in his lap. She attempted to swivel from her mount, until the boy's hands rested firmly on her waste, trapping her. "How many do I have now?"

"34!" She retorted, unable to keep her half laugh behind her teeth. "Now knock it off while I finish counting."

"Knock what off?" He mocked before pecking her on the lips. "I don't know" the cheek, "what you're" the other cheek, "talking" the chin, "about" below the chin. As Ruby struggled to keep her line of slight straight, Oscar relished as he began trailing more small kisses down her neck. The girl in his lap squirmed and giggled as she tried with every fiber of her being to keep counting.

"39… 40… 41, 42- hey!" A bit of breath was sucked out of her as Ruby felt Oscar nip at her collar bone after fiddling with the fastenings on her hood, making it fall to the ground showing her exposed neck.

"How many do I have now?" Oscar whispered into neck while nuzzling it.

"42, 43-"

"How many?" His grip on her tightened, pulling her closer allowing him to caress her jawline with his lips.

"44! 45! 46! 47- AH!" Ruby suddenly felt her body being torn down, bouncing against the couch cushion as Oscar trapped her under his hold, kissing her much more feverishly.

"Didn't quiet catch that?" his voice was thick with mischief, and an almost uncharacteristic huskiness that Ruby couldn't help but be slightly enthralled by. Until she felt the hands at her waist brush and dance at her sides, causing her to erupt into howling laughter.

"Wanna repeat that for me?" Oscar snickered as he tickled Ruby mercilessly. Squirming under him she fought to find the numbers she had in her head but a moment prior, but lost them somewhere in the bubbling laughter and flurry of smooches.

"HAHAHAHAHAH- I-I- I DON'T KNOWHAHAHAH! I DON'T KNOW! PLEASE! NO MORAHAHAHAHAH!"

That's all he needed to hear. With a quick kiss on her forehead the feared tickle attack ceased, leaving a breathless and slightly flustered Ruby. Oscar couldn't help but smile and admire his work, seeing such a beautiful girl in such a blissful state simply because of him, it brought his heart close to bursting. Ruby stared back, feeling a similar emotion.

Oscar lowered himself, cupping his hands on either side of Ruby face before kissing her. Her left hand clutched to the fabric of his shirt while the other ran through his soft hair, causing him to sigh contently into her mouth. Despite the feverish tussle from a moment ago, there was a different type of passion behind their kisses now. A much deeper, much more intimate one. Oscar felt Ruby's tongue slip between lips, moans dribbling out by the corners of their mouths, lost in complete, and total pleasure.

There was a loud knock at the door, and a sudden burst before either of the youths could respond. Stumbling in, filled flask in hand was Qrow, obviously drunk given his wobbly posture. He leaned against the door frame, mouth agape as if he was about to speak, then stopped upon realizing the situation his beloved niece was in. Both teens froze, caught like deer in the headlights, Oscar still very much laying on top of Ruby.

"Don't… worry." Qrow slurred, reaching behind his back fumbling for his sword. "I'll be sure to shoot you first… _before_ gutting you."

Ruby looked up to Oscar with a look of pure horror. His hazel eyes darting between Ruby and Qrow.

He whispered a quick "Let's finish this later" before pushing himself off the couch and daringly leaping out the window. Qrow followed in pursuit but ended up running into the wall next to the window instead before taking the long way around back down the hallway.

…

63\. He had 63 freckles.


	4. Chapter 4: First Time

Ruby recalled the first time she had been given 'the talk.' Back at Signal Academy, she had asked her father about a strange vocabulary her male peers had been using. Tai Yang avoided the answer like 'a class A ninja' as Ruby had described it, but her dear big sister was kind enough to fill in for him. Looking back on it now Ruby was thankful it had been her sister rather than her dad, and now understood his need to stay discrete. But she never thought she'd ever be thankful to Yang for tossing that small silver packet to her in joking jest, or for hanging onto it for so long for no reason other than she didn't know what else to do with it.

Oscar had no transition, or a sibling to fall back on, he had simply walked into the kitchen one night with his aunt sitting him down and simply stating "Let's talk about sex." Poor kid was only twelve when he was told about the workings of male and female anatomy, not that he ever really needed to worry about things like that. He and his aunt lived practically in the middle of nowhere after all.

And that leads to right now, Oscar and Ruby sitting face to face on plush mattress in a darkened room. Thanks to the sudden interruption by Ruby's drunken uncle a few hours prior, the mood currently had a palpable nervousness that hung in the air like a gas as opposed to their friskiness from earlier that afternoon. But Oscar was taught to be a gentleman, and a gentleman never goes back on his word, nor fails to finish what he started.

He recalled his promise. _"Let's finish this later…"_ And now was starting to question his choice of farewells.

"So…" Ruby twiddled her thumbs, keeping her stare there. "I don't suppose, you have any idea how this works…?"

"Not really." Oscar distracted himself by scratching the back of his head. "You?"

"Well I mean… I've read books! Though I'm not entirely sure how accurate a romantic ninja mystery novel would be for something like this." Ruby blushed, with Oscar following suit. They both had figured a night like this would come around eventually, but it had been nothing like they expected. There wasn't much of a buildup, and it felt natural but it just seemed so spontaneous and spur of the moment. Perhaps this is how most of these things started?

Oscar took Ruby's hand in his, rubbing his thumb over the top of her knuckles gently as if trying to convey his intentions and feelings into one gesture.

"Are you _sure_ you want to do this?" He inquired. "I don't want you to feel like you have to or anything. I'm fine with waiting."

"Well… do _you_ want to wait?" She inquired back.

"I…" Oscar blushed, closing his eyes for a moment before looking at Ruby calmly. "I want whatever you want. After everything I've gone through, you're the one thing that happened to me that I never regretted. Not even for an instant." Oscar squeezed her hand. "I want you to know you are my everything. So whatever you want, I'll honor that choice."

"I want…" Ruby looked at him almost blankly for a moment, then at their now intertwined hands. Her gaze softened, showing less signs of contemplation, and more of a tranquil certainty. She blushed upon stating: "I want you to take your shirt off."

Oscar felt his breath hitch and his face heat up. His heartbeat quickened by the second as he looked at Ruby, who silver eyes portrayed something like an innocent certainty. And who would he be to not follow through for his one and only? His hands grabbed at the back of his collar pulling over his head in one swift tug. He tossed the shirt aside, returning his gaze to Ruby who now inched closer to his exposed chest.

Her palms rested on either of his pecs, thumbs tracing his collar bone, Ruby could even feel his erratic heartbeat. Her right hand glided up his neck, rested at cheek and gently pulled him closer. The kiss was soft and sweet, much like their first, but burned with a passion like neither had experienced before. There kiss deepened, their holds tightening around each other. Ruby's hands ran up and down his biceps as Oscar held her by the waist and lower back. Neither of them is certain who's tongue runs along their bottom lips first. An insignificant fact as both mouths open allowing either to roam freely.

Oscar, rummaging around the hem of Ruby's shirt, slinked his hand under the hem so that his hand rested on her bare back. Her skin felt as smooth as he had always envisioned, he felt her heart beat through her shoulder and the lace that lined her bra. She had begun to trail kisses down his neck, making him shiver under her touch when a sudden boldness clouded his conscious as he decided to remove her shirt as well. Oscar clutched the fabric in his hand, attempting to pull it over her head. Ruby retracted, but grunted a bit as the shirt caught at her shoulders. Oscar tugged again, the shirt not quite budging like he had hoped. Ruby quickly squirmed from his hold muttering a quick 'let me do it' as she removed her own shirt in one fell swoop. And just to make up for the fumble, she shimmied her way out of her skirt as well.

The freckled boy swallowed hard as Ruby sat before him, dark lace underwear highlighting her pale body. Oscar was certain in that moment that she must have been a goddess, or an angel of some kind. There was no way any girl in the world could be this beautiful. It was his turn now to work at her neck, kissing her from her lips, to her jawline, down her neck, at her shoulder, around her collar. Ruby sighed contently he kissed her, her massaging the roots of his hair as his hand fumbled at the clip of her bra.

Red and black lace fell into Ruby's lap as a chill passed over her now bare chest, Oscars hands making quick work of their presence. He cupped her breasts, massaging and kneading at them as he nipped at her ear. Sighs of content dribbled from Ruby's lips, signaling to Oscar to continue teasing her with his teeth. He bit at her shoulder, a bit too hard in his daze as he soon realized upon hearing Ruby let out an audible "Ow…"

"Sorry!" Oscar quickly sat up, stroking Ruby's cheek and then ducking again to kiss the bite mark. "I wasn't thinking."

"It's okay." She laughed, kissed him deeply, and ran her hands down his side until she felt the rim of his pants. Her hands fumbled with the buckle of his belt, the tinkling of metal filling the room as Ruby's eyes averted to focus on the hem.

"Do you need help-?"

"No." She stated it so matter-of-factly, though it seemed obvious by her still struggling hands that that wasn't the case. Oscar contemplated helping her, but decided that may only complicate the situation further. She eventually got the thing unhooked, and it was at that point that Oscar decided to help her slip off his pants. What he had not expected her to do however was so quickly grab at the hem of his boxer briefs and tug them down as well. His only in-time response was a small gasp.

She couldn't help but stare. Textbook diagrams were one thing, but to see and actual guys… in real life… and Oscar's no less… She wasn't saying she thought it'd be small but… _that's how big they typically are?_ And the fact that it just… stood up…

"Ruby are you okay?" Looking up she saw that despite his incredibly beat red face, Oscar looked genuinely concerned at her sudden stillness. It almost resembled a look of fear. She swallowed hard, her face feeling as hot as Oscar's looked.

"I… um…" she stammered, her eyes darting between Oscar and his… "I-I don't know…what to do with… this." Ruby felt the claws of mortification crawl up her back, making her only redder.

"Just call it a penis, Ruby. It's less awkward if you don't avoid it." She gave him a look that resembled an angry pout, puffed out cheeks and all. "… you can… touch it if you want."

With shaking hands, Ruby's fingers traced along Oscar's member, trembling under her touch. Neither had any idea quiet what was happening, but Oscar's hitched breath only made Ruby assume she was doing something right. Her fingers wrapped around him, gently stroking up and down, her speed steadily increasing as his breaths grew heavier. Ruby found herself tightening her grip around him also as the speed of her strokes increased until she held him by her fist. She gave one hearty tug, only to quickly withdraw when Oscar's response was a pained yelp followed by him clutching his crotch.

"Crap! I did it wrong! I'm sorr-"

"No! No it's fine!" his voice was strained but sincere. "You- you're doing awesome…"

Ruby crawled onto his lap, kissing his head, noes and lips as her form of apology. Oscar complied by rubbing her back reassuringly with one hand, the other resting at her bum. He slowly started to rock her, at first in compliance with the kisses she had been leaving him all over his face. But as both took notice of their jutting hips with each rock they steadily grew into something of a light grind. Ruby held Oscars shoulders, chomping on her lower lip as she felt his penis harden and rub under the lace of her panties. He picked her up slightly, laying her down on her back only to quickly ravish at her mouth and hook his thumb at the band of her underwear.

"Wait… Wait hold on!" Ruby exclaimed, slightly short of breath. Oscar sat up, allowing Ruby to crawl off the bed to were her skirt had been tossed aside. She rummaged through the pockets of black fabric before pulling out the small silver packet.

"Here," Ruby handed the packet to Oscar "you know how to do this right?"

"Umm, sure." At least he thought he did. He peeled the wrapper back holding the condom by the ringlet. He brought the rubber to the top of his member, feeling a slight tinge of panic when it would not budge from its mold. He flipped it over, almost dropping it knowing Ruby's eyes were on him. This time the condom unraveled as Oscar brought it to the base of his crotch.

"Are you… certain?" Oscar asked, his voice shaking just a bit. Ruby responded with a nod, and kissing him softly. The young man hooked his fingers around the hem of her underwear, sliding it down her thigh until Ruby eventually kicked it off with her own feet as she laid herself down.

Even with the slowness of his insertion, Oscar couldn't help but shudder at the sudden sharpness of Ruby's breath. She bit her bottom lip as more unpleasant whines escaped through her nose, more of her breaths shallowing.

"S…Sta…" her barely audible whisper resembled more of a pained plea.

"Stop?" he frantically replied "Do you want me to stop?"

The immediate shaking of her head was as frantic as his question, and hadn't fully convinced him that that had been the full truth. But following her stead he slowly slid the rest of himself inside her until their hips met. After that he stood perfectly still above her, not daring to move.

"Are you okay?" he asked, swiping a small strand of ebony hair from Ruby's eye. She opened one eye, squinting up at him.

"Yeah…" she attempted a smile, her words breathless. Oscar may have believed her words had they not been immediately followed by a single trickling tear down her right eye. The boy's heart came close to shattering.

"Okay no. No, I'm not." Ruby caved as a few more tears escaped either eye. " _Shit this really hurts…_ " Oscar was quick to close what little distance was between them, an ultimate wave of guilt washing over him.

"Damnit! I don't know what I'm doing, I'm sorry!" He held her face in his hands, attempting to kiss away the tear tracks on her cheeks. He had wanted to make Ruby's first time special for her and here he was royally fucking it up big time. The fact that he alone was causing her this much pain, it hurt him more than anything. "I'm sorry, I'm so sorry. I love you so much, I'm sorry." He continued coaxing her kisses, massaging the roots of her hair to calm her down.

Ruby gripped Oscar around his neck as he continued to whisper sweet nothing's in her ear. She felt embarrassed, but was grateful for Oscars desperate attempts to accommodate her. After a few minutes her breathing steadied, her grip loosening and the pain of their intimacy nulling. A small hum of contentment escaping her lips as Oscar continued to stroke her hair.

"Move…" she mumbled into his shoulder.

"Hmm?" Oscar felt her hands slide down to his hips pushing them just a bit before pulling them back again.

"Move." Her voice was affirmative, letting Oscar know she was certain.

Their two bodies gently rocked back and forth, hips jutting as they reached a steady rhythm. Both felt that they weren't doing this thing correctly, but as tiny pulses of pleasure rippled through them the longer and slightly faster they went, both realized they didn't really care. Despite their mishaps, and childlike confusion, in this moment Oscar and Ruby were closer than any other human being they had ever known. It would not go down in history as a perfect moment, but the moment was theirs all the same.

Ruby had never experienced anything like an orgasm before. She remembered her insides tightening before feeling the rush of a sudden hot wave, feeling a bit embarrassed that it had left a wet spot on the sheets beneath them. She had felt it in Oscar too, the fluid of his ejaculation trapped by rubber as he stiffened. Their bodies shook for a moment as the shock of their sudden spasms washed over, leaving the two in a tranquil peace.

Oscar collapsed next to Ruby, his arms wrapping around her as he nuzzled his face into her hair.

"Was that… terrible?" he asked between exhausted heaves of his breath.

"Not entirely."

"But a little bit?"

"Yeah" Ruby snorted, her head resting at the crook of Oscars neck. She felt him pull a blanket over them, now noticing she had been shivering a bit. Whether that was from the temperature or their intimacy was a different question.

"I love you." He had whispered it just before her eyes fluttered closed. Ruby felt the slightest tinge of guilt not having the energy to say 'I love you too,' hoping a single 'Mmm hmm' would suffice, which it did.

Ruby and Oscar both slept peacefully, though not without a few very bizarre dreams afterward.


	5. Chapter 5: Morning Routine

Note: Established Relationship- Rated F for Fluff

The day was calm and peaceful, accompanied by the soft song of birds and a gentle breeze. Sunlight peaked through the curtains, a beam of yellow falling on Oscar Pine's face. His eyes fluttered open, hazel orbs meeting the shine of the sun and squinting under it. The palm of his hand rubbed the flakes out of his eyes and glanced at the clock by the bedside.

10:03 am. He never usually woke up this late, around this time on any other day back on the farm he'd be finishing his late breakfast and continuing his morning chores after washing his dish. Even in recent days his morning typically started around six or seven. But smiled contently anyway, slightly enjoying the bit of extra rest he received.

His attention then turned to the ebony haired girl sleeping beside him. The same sunray from before glowing against her pale skin. The blankets draped over her body perfectly sculpting her form as her breaths quietly seeped in and out. Despite the tiny track of drool spilling over her lip and staining her pillow, Oscar couldn't help but sit and stare at her in awe. Truly he must have been one of the luckiest men alive.

As he stretched out his arms and legs, sheets shifting over him he turned on his side to face the girl next to him, arms snaking around her waist.

"Ruby?" No response. "Ruuuuuuby?" The only response he received was the tiniest of snores escaping her lips. Oscar couldn't help but chuckle. He set his forehead against hers, still earning little to no response. "Ruberry, we gotta get up." Despite shaking her just a bit, she still only snored in response leaving Oscar to shake his head in disbelief. It was incredible how heavy of a sleeper Ruby actually was, but damn it all if she didn't look adorable while doing so.

Oscar brushed a small strand of hair from her face before planting a kiss on her forehead, just about ready to give up on his endeavor and let Ruby sleep in. Before he could toss the sheets off him however he caught a small sigh passing through her nose, her mouth just slightly twitching into a smile for the quickest of seconds. The boy grinned to himself.

He inched as close as he could before planting a kiss on her temple, followed by her cheeks and noes. Her face shifted each time Oscars lips brushed her skin, seemingly as if trying to break out of a deep slumber. A small trail of kisses along her jaw left the girl stirring, audible responses aside from snores finally emerging from the depths of her throat. Oscar tilted his head, kissing her under her chin and along her neck as he felt her own body shift beneath the covers. There was a small grip on his pajama shirt, and soft hum from Ruby indicating she was finally awake.

Oscar lifted his head, laying it next to Ruby's on her pillow. She had a much wider smile on her face now.

"Good morning, Ruby." He waited until her eyes peaked opened before leaning in to kiss her properly, her breath tickling his nose.

"Morning, Freckles" she ironically replied as she buried her face in the crook of his neck.

"Anything in particular for breakfast this morning?" Ruby hummed in contemplation, eyes closed again in relaxation.

"Hmmm… waffles."

"With eggs and sausage?"

"Eggs and bacon." Oscar looked down at her, an amused expression on his face.

"We can't be having bacon with everything, every day, Ruby."

"Bacoooooooon!" Her protest was enough to make Oscar chuckle, kissing her forehead one more time before peeling himself from Ruby's grasp, folding the blankets of the bed off him and slowly making his way to the door.

"You coming?" Oscar asked, looking back at his girl still sprawled out on the mattress.

"In a bit… just give me a minute."

"Okay, don't take too long." Before he could make his way out the door he turned one more time upon hearing Ruby mutter his name once more. "Yeah, Ruby?"

"I love you…" The words are almost lost in the cotton strands of her pillowcase, but Oscar smiles upon hearing her words anyway.

"I love you too, Ruby-roo."


	6. Chapter 6: Alone

A lot of things were fading away around him. The corpses of the grim they had slain now faded into black clouds like ash, the light of the sun from beyond the horizon now faded as cold colors seeped into previously warm ones, even the edges of his vision blurred just the slightest bit from the exhaustion of the fight. Oscar saw many things fade in front of him, but he felt only one.

" _Oscar…_ " his head rose slowly, as Ozpin addressed him. He had grown so used to his presence within the caverns of his mind. For months acting as a voice of reason, direction, but most importantly a teacher. The two, despite the unfortunate circumstances of how they met and why, formed something of a close comradery. Much like a student to his pupil, or even, dare he say, a parent to their child. Their bond was closer than something Oscar could ever explain, but as of right now, he could feel it…

" _You've done so well, Oscar_ …"

…He could feel it fading away.

" _I'm afraid, we've run out of time…_ "

"What are you…?" Oscar tried speaking to the old soul, not even attempting to refrain from speaking out loud as a twinge of panic grabbed at his chest.

" _I want you to know that I never had any doubts in your abilities. I knew you would do wonders, and I can certainly say you did not disappoint._ "

"What are you talking about?"

" _My only regret is that I didn't stick around long enough to see what else you would achieve_."

"Stop talking." Oscar attempted to address him, sternly as if scolding Ozpin much like he had him in the past. But the old voice continued, as if Oscars words fell on deaf ears.

" _The challenges you and the others are about to face, they will most certainly be challenges greater than anything you've faced before. There will be times you may feel lost, or confused, even hopeless. But I know whatever choices or actions you make, they will be the right ones_."

He could feel him slipping away, like his head became lighter and lighter by the second.

"Ozpin, don't!"

" _It's okay, Oscar._ " The boy fell silent " _My memories are yours now. As is your fate_." Ozpin's voice grew duller and duller. " _I'm proud of you Oscar… good luck…"_

All at once, a sudden peace fell over Oscar's trembling form. His pounding headache from before ceased, his muscles relaxed, a sudden flood of memories and emotions surging through him. It almost pained him, if only for a split second before seeping into the depths of him. He felt different, but he hardly cared. His mind felt cleared, and it terrified him.

"Ozpin…?" There was nothing. Only silence surrounded the boy, the wind being the only kind thing to reply. "Ozpin?!" His voice echoed in the openness. "Knock it off! This isn't funny!" A beowulf's final growl escaped its lips as the remainder of its form faded into smoke. "You can't leave! Not yet! Please!" The fluttering of a bird's wings passed over the silence, but nothing remained.

Ren and Nora were the first to find Oscar, and could faintly be heard calling the others over to them, but Oscar paid them not mind.

"OZPIN!" his throat grinded as he screamed but he didn't care. "You need to stay! I don't know what I'm doing! You're the only reason I got this far what am I supposed to do if you're not there to help me?! Please say something! Anything! I don't know what to do! SAY SOMETHING!"

. . .

It was strange, he had recalled feeling this way before. A thousand lifetimes worth of loss and sadness repeated over and over though generations that weren't his. He knew this pain, yet he didn't, it was something he felt all too often, yet nothing like he had ever experienced before. He couldn't help but weep. And the fact that his sobs were the only thing he heard, the only thing he felt only pained him more.

Jaune and Ren took turns carrying the boy, his form completely and utterly exhausted. The team worried for him, with even more following suit when they met up with their comrades from team RWBY. Oscar took comfort in the friends around him, as they regrouped in the nearest town, planning their next advancement.

Ren was the first to ask what had happened to Oscar during the fight, and the boy was careful with his words so as to not choke on them as he explained. He began curling in on himself, as everyone's faces turned to him with a look of grievance, and something that resembled pity. He noticed _her_ face didn't seem that way though, that she didn't look at him with pity… It soothed him for a moment, but only a moment.

Their mentor was officially gone for good… and it left a feeling of dread and uncertainty in each of their stomachs.

When the teams retired to their rooms, Oscar dreaded the thought of rest. In the darkness of his small room, he felt like he walked in an abyss. He tried to sleep, he tried to rest, tossing and turning and scuffling his bedsheets, but the quiet was surprisingly suppressing. For months he had grown used to Ozpin's presence, knowing that whatever the unknown held for him the next day or just around the corner, he would be there to explain, to offer solutions. Perhaps the old man was something of a crutch, it certainly didn't change the fact that he felt lost and utterly alone without him there.

He got up, and wandered the halls of the inn like a ghost. He hadn't bothered to put on his boots, so the floors barely creaked as he paced back and forth from one end of the hall to the other. The numbers on the doors counted up and down with every which way he walked, small slivers of light just barely seeping into the dark hall from the rooms behind mahogany doors.

He found himself standing in front of her door, he knew she was awake because the light from inside shined through the hinges. He hesitated, wondering how intrusive his actions may come across. He had made many friends on his journey, but of all of them she was always the one who saw him for who he was. She always saw him as Oscar Pine, not Ozpin, not Ozpin's successor, not the chosen one, or wizard, or whatever title had been passed down to him through his many past lives, just Oscar.

He ran his tan fingers through his messy black hair before knocking on the door, loudly enough to insist urgency, but quiet enough to not wake up any neighboring guests. He heard soft footsteps from inside inching closer and closer to him, followed by the quick click of the door's handle as warm lamp light washed over Oscars form. Her silver eyes met his, her expression knowing.

"Hey, Oscar." She greeted quietly.

"Hey, Ruby." He responded, even more quiet than her greeting had been. Ruby recalled first meeting Oscar, his very being was much more reserved back then. Looking at him now, 'reserved' didn't even do justice just how withdrawn and scared he seemed. After seeing how much he had grown but a few days prior, she hated seeing her friend like this.

"How are you doing?" She felt she knew the answer, but asked regardless.

"I'm not okay." The matter of fact tone to his answer was enough to make her chest tighten, and his averted gaze down to the floor even more so. "For months, I had been living with the voice of an old man in my head. Telling me what I was supposed to do, expect, and who I was supposed to be. I hated it at first, but at the same time he was the only one who made sense of everything happening around me. These memories, these abilities, he always said they were meant to be mine… but deep down I always felt like they weren't. Even now I have thousands of years of knowledge and memories stirring inside me and I have nothing to make any sense of it! Or anyone!" His voice began to crack, Ruby gripping the door frame unsure if whether she should take hold of him or not. "He always said 'this is how things were meant to be'… So why do I feel like a piece of me is missing if this is what being whole is like?"

"… Oscar, what do you need?"

"I just…" He finally looked up to her, his eyes reflecting an emotion that could only be described as desperation. "I really don't want to be alone tonight."

Ruby nodded, she may not have understood his predicament completely, but she did know what loss felt like, and isolation was never a good thing to pair with it. She gently took Oscars hand and lead him into the room, the door closing behind them.

She sat herself down on the bed, Oscar sitting beside her. Ruby hadn't even adjusted the pillows for two before she noticed the boy's shoulders shaking rapidly. She lifted his hunched form, revealing the fresh stream of tears staining his cheeks.

"I-I'm sorry…" his words hiccupped. "This must look so pathetic…"

"Oscar…" Ruby pulled the boy closer to her, until his head rested in the crook of her neck. "It's okay."

Another wave of tears leaked through his shut eyes, his breaths growing shallow and hitched. Oscar clung to Ruby, crying into her shoulder as she stroked his hair and rocked both of them back and forth. She recalled being held like this by her mother, and sometimes Yang on rare occasion, it felt somewhat strange to be the one doing it for once. But if she was being honest with herself, for Oscar, she would have done anything to ease his pain.

"I'm terrified Ruby…" he mumbled into her shoulder "I don't want to be alone." He suddenly felt her chuckle a bit as she massaged his scalp.

"Oscar, you're so silly you know that?"

"What do you-?"

"You've never been alone." The girl's forehead rested on top of Oscar's, providing a new type of closeness as she soothed him. "Even while Ozpin was still with you, you always had friends willing to help you. Uncle Qrow trained you, Jaune, Nora, Ren, your team befriended you. We met…" Both took notice of the emphasis she spoke with on 'we.' "And not just because you're Ozpin's successor or whatever, but because of you. Oscar Pine. One of the bravest dudes I've ever met. I may not know the full story, but I feel like Ozpin knew you'd be okay, because if you ever feel lost and afraid, you'll have us to fall back on. Do you understand?"

Oscar slowly looked up, his eyes still damp and glossy, but his expression had shifted. He no longer looked up to her with sadness, in fact Ruby wasn't certain what his expression actually was. She just knew it bored into her, making her feel like she'd melt under its gaze

"How… are you always like this?" he asked, almost whispering it.

"Like what?"

"Just… perfect in every way." Ruby felt her heart skip a beat, the smallest sense of elation spreading through her. Her face must have reflected it as she watched Oscar's shift to a shyer half smile.

Neither of them is sure who leaned in first, just the sudden recognition of their breath on each other's lips was all they recalled before gently kissing one another. Before closing her eyes completely Ruby could have sworn she saw one last tear roll out from the corner of Oscar's eye.

Oscar snatched either side of Ruby's face, deepening the kiss in a mixture of passion and longing for closeness. Both of Ruby's hands took hold on Oscar's neck, pulling and keeping him closer, rubbing at the nap below his hairline. Her touch was like hot iron on ice, melting him. His scent reminded her of pine trees and open fields, hers filled Oscar's senses with the scent of dust powder and roses. She admitted feeling his desperation. Despite the multitude of kisses being perfectly plentiful and feverish, each felt more like a small cry for help than a gesture of passion. Like he had clung himself to precious thing he was terrified of losing. It was flattering to say the least, and Ruby was more than willing to be there for him.

The two stayed that way for a while, a few stray tears streaking down Oscars face every so often. Ruby would break away to wipe them away with her thumb or kiss the streaks left behind. They took comfort in the taste of one another, leaving previous doubts and worries to the wind. Ruby's hands glided up to Oscar's shoulders, and could feel the tension loosening. The feverish kissing from before slowing into smaller pecks. Ruby pulled the two of them down until both rested on their sides on the bed.

"I assume you don't really wanna head back yet, do you?" The boy only hummed in response, shaking his head ever so slightly. The ebony haired girl pulled a large throw blanket over the two, scooching over so that her bedmate may have more room.

Oscar immediately wrapped his arms around Ruby's waist, holding her like a child's first bear. Ruby sighed contently, resting her head now in the crook of Oscars neck. She could feel sleep gripping at her consciousness as her hand rubbed circles on his back, making him let out a calmer but still a bit of a shaky breath.

"I love you, Ruby…"

She was certain he could feel her heartbeat accelerate through her chest as his grip around her tightened a bit. She couldn't help but smile like a dope, and had she'd been more awake, she might had tried to conceal it. She kissed his chin before replying.

"And I love you, Oscar Pine."

Oscar had gone to sleep afraid of the inevitable bombardment of nightmares he was sure he'd receive, but in her hold, he felt safe, and gentle rest soon followed.


	7. Chapter 7: A Question

"Keep them closed. We're almost there" The elevator doors slowly slid open, and Ruby stepped forward hesitantly as Oscar kept his hands over her eyes as they walked.

"I hope so" she giggled "Walking around this much without seeing anything makes me nervous."

"Okay one second!" Oscar lifted his left hand slightly, making sure Ruby's eyes were still closed beneath them. Upon seeing her shut lids and slowly removed his hands from her face, backing up some. "Alright, open your eyes!"

Two silver orbs were greeted by a dazzling orange light. Looking around Ruby soaked in the room they stood in, a familiar office she had visited multiple times in the past. Last time she had been here, it was in shambles and piles of rubble. Now it stood proudly in one piece, the gears of the tower placed properly once again, though none of them were in motion. And the glass of the windows polished to perfection, giving the two the perfect view of Vale's sunset.

"No way! This is Ozpins- I'm mean your- or the headmaster's old office!" Ruby stammered.

"You know I don't care which term you use right?"

"It looks good as new! And the windows…" Looking over the windows again, she noticed the orange glow wasn't just from the sun. Each pane was accented with bright orange stained glass, glowing bright and warm into the room.

"My personal touch." Oscar chimed, a hint of pride in his voice. "I figured, a new era in Beacon's legacy and all, it should look the part." The two young adults made their way to the window itself, looking out on its breath-taking view.

"It's gorgeous!" Ruby took hold of one of Oscars shoulders, pulling him close into a playful hug. "I'm sure the rest of Beacon will be too." She smiled up at him, making the boys heart flutter.

"It's exciting getting to see it build into something new. Hopefully maybe something bigger and better than before. The whole being headmaster thing still is kinda throwing me for a loop though." With the death of Beacon's former headmaster, it only made sense for his successor to be… well his successor. Despite his youth, he had years' worth of experience and leadership from the memories of his past lives. As the wizard, he was more than qualified, but as Oscar Pine he felt a bit over whelmed.

"I wouldn't worry, you'll make a great headmaster I'm sure."

"I hope so…"

"I know so." Ruby leaned her head against Oscars shoulder, allowing him to rest his atop her head.

They stood there and watched the sun, occasionally looking down at the construction workers and machines down below who even now worked to rebuild Beacon Academy to its former glory. After defeating endless hordes of grim, and even a wicked witch of sorts, they felt incredibly lucky to have made it this far, Oscar especially. Ever since merging with Oz he had been told that the odds would not be in his favor. The chances of him surviving were slim, the chances of all his friends surviving even more so, the possibility of ever being with Ruby Rose, nonexistent. Yet here they stood, both alive and well. He could hold her hand, stroke her hair, and kiss her senseless if he wanted. He felt more than lucky, he felt blessed.

"I want to be the best headmaster I can…" Oscar shifted to an upright position. "But I've also been talking to Glynda and Ironwood about other things…" He gripped the old cane in his hands.

"Oh?"

"They both agree that my life shouldn't be dictated by what Ozpin left behind, that I should be allowed to live my own life. Finding hobbies, settling down, starting a family. Ozpin never had a life like that, I think he felt obligated to commit himself to a life of solitude." Oscar recalled the memories of Ozpin's life as if they were his own. Emotions and all. "Personally, I don't think that's fair, to his loved ones or himself…"

"Yeah, I can see that…" Ruby agreed, not fully understanding but understanding all the same.

"But I don't want to live that way, and I don't want any future wizard to feel like they need to live that way either. So maybe by living a simpler life, and can convince future generations of wizards that there can be balance to duty." His gaze was far away as he spoke, and not once during his whole spiel had he looked to Ruby. Realizing this his head whipped around to meet her gaze his expression once again very present. "Oh sorry, I was rambling there."

Ruby giggled, bumping his shoulder with hers in teasing jest. "Don't worry about it."

"I promise there was a point to this." Once again, his gaze shifted, down to the floor this time. His expression hardened, as if he was uncertain of what exactly his next words would be. "That point being, I want to live a life of my own, as Oscar Pine. Not just the wizard. And… you see…" he swallowed hard "I… I'd want nothing more than to able to share that life with you… Ruby Rose."

"Oscar… what are you-?" she had little to no time to ask her question as Oscar suddenly faced her, clutching her hands in his.

"Ruby. I've been so madly in love with you, from the first moment I met you. Ozpin told me multiple times falling for you was a bad idea, not to mention Qrow threatened my life multiple times! But I knew! I knew falling in love with you when I did, despite how reckless it may have been, I never regretted it. So I wanted to ask you properly…"

His legs shook slightly under him as he brought himself down to one knee, never letting go of Ruby's hand. She felt her heart accelerating, she felt breathless.

"Oscar…"

"Ruby Rose, would you share your life with mine, and become Ruby Pine?" He reached into is breast pocket, and pulled out a small gold ring. Its single diamond glittering in the orange light illuminating the small roses engraved in its band.

"Will you marry me?"

"YES!"

"You wi- GAH!" A sudden burst of rose petals surrounded the two as Ruby tackled Oscar to the floor. She acknowledged his grunt of pain as they hit the floor, but she hardly cared in her excitement.

"YES! YES! YES! YES! YES! YES!" She gripped his neck in a fierce hold, shaking his form slightly as she kissed his face up and down. She pecked the center of his cheek, recoiling when she suddenly tasted salt on her lips. Ruby looked up noticing multiple tears streaming down Oscars cheeks. "Oscar are you okay? I didn't hurt you too bad leaping on you did I?"

"It's just…" His hand swiped at his eyes, ceasing the flow of fresh tears as he looked up at Ruby, smiling brightly. "Hehehe… I'm just so happy!"

The two beamed at one another, kissing each other on the lips before resting their foreheads against each other's as Oscar slipped the small ring on Ruby's hand, the small silver diamond glistening.


End file.
